


Starting Line

by spiralicious



Category: Supernatural
Genre: Crossdressing, Insecure Dean, M/M, stiletto race
Language: English
Status: Completed
Published: 2016-06-24
Updated: 2016-06-24
Packaged: 2018-07-18 01:44:54
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 762
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7294501
Author URL: https://archiveofourown.org/users/spiralicious/pseuds/spiralicious
Summary: <blockquote class="userstuff">
              <p>Sometimes you win the race no matter how badly you run, or Dean's social experiment on crossdressing within the confines of the gayest environment he could find.</p>
            </blockquote>





	Starting Line

Sam stopped short. He had gone to look for Dean, as soon as he realized he was not with the other contestants at the starting line. He had backtracked to the car, figuring his brother was still getting ready. Sam had known that the stiletto race involved cross-dressing, but that still did not prepare him for the sight before him. 

“You are so never allowed to call me Samantha ever again.”

Dean looked up at that with wide eyes. He had given this second, third, fourth, and twenty fifth thoughts. 

“Shut up.” Dean backed up closer to the Impala with nowhere to hide himself. Logically, he knew that there would be others more dressed up than himself and it had been his idea to join the race, but it just felt so weird doing this in public. 

“You look good,” Sam reassured him as he quickly started closing the distance between them. He meant it. Dean wasn't wearing anything that outlandish. He'd cut an old pair of jeans into short shorts and was wearing a black t-shirt and some light make up. Sam had seen the other race contestants. The only reason Dean might stand out was his tameness. 

Dean had practiced in the black heels he was wearing for days. He still wasn't sure he could actually run in them. It was a stupid idea, but when he found the flier it had seemed like the perfect way to celebrate his, their, new freedom. Dad was dead, heaven didn't need them, hell wasn't after them, and there was no one left who he gave a flying crap about their opinions, besides Sam and Bobby. Bobby didn't really ask questions or care what he did as long as he wasn't hurting himself or Sam, or doing something incredibly stupid, like opening a hellgate or something. Sam, he had been expecting more teasing from, not about the being bi or whatever he was (Dean was not ready to slap a label on that yet), but about the sort of cross-dressing thing. Dean didn't really know what he liked in that regard. What little he had indulged in had been small and secretive, like wearing panties and getting rid of them, or stealing a lip gloss to only wear when no one was around. When Dean had finally realized he no longer gave a crap what people thought and decided to bear his soul to his brother about his wants and fears and predictions, Sam had just looked at him with that face he reserved for when he thought Dean was really stupid and told him, “Dude, I know.” Dean had been both infuriated and comforted by the response. He still only tried little things here and there, but feeling free enough to experiment, at least in front of Sam, was very freeing. This crazy-assed race was all together different. It was in front of people. There was a crowd. Sure, Dean didn't know anyone there, except Sam and Bobby. Virtually everyone there was crazier than him. He also kept reminding himself that he didn't give a shit what anyone else thought of him. Except, he kind of did.

“Dean?”

“What?” He was a bit startled that his brother had closed the distance between them without him noticing. 

Sam pulled him into a crushing hug. “Go kick some ass.” He punctuated the statement with a very unbrotherly kiss. 

It was Dean's turn to be shocked once again. “What the hell, Sam? What if someone sees?”

Sam's bitch face was epic and instantaneous. “We're two men in the parking area of a gay pride event. I don't think anyone will be shocked.”

“But we're...”

“Together?” Sam cut him off. His facial expression begged Dean to be slightly smarter.

It suddenly occurred to Dean that Sam had been cutting him off and preventing him from introducing him as his brother all weekend. Maybe this weekend was a bit of a celebration for Sam too. “But Bobby is...”

“Waiting at the finish line for you and trying to keep that pushy woman from trying to recruit him for PFLAG.”

Dean straightened up. He could do this. He took several confident steps away from the Impala before he felt a very large hand swat his ass. “I'm not sure I'm liking this more assertive side of you, Sammy.”

Sam speed walked passed Dean. He could tell from his little brother's shoulders that he was smirking. Tonight, in the hotel room, Dean was going to wipe that smirk off his face, but first he had a race to win.

**Author's Note:**

> Thanks for pinking, Kira and Jen!


End file.
